2000 Luella’s ‘Daddy I Want a Pony’ T-shirt
Journalist, designer and all-round British fashion legend Luella Bartley launched her eponymous label in 1999. Inspired by English culture, from punks to the Pony Club, she rose to fame in the Cool Britannia era and her irreverent logo tees became signifiers of effortless chic. Her first ever collection, presented in September 1999, was entitled Daddy I Want a Pony, and when the label shuttered ten years later, this iconic T-shirt became an important piece of fashion history.
2001 Jimmy Choo sandals
Sex and the City fans will vividly recall the episode where Carrie Bradshaw calamitously makes a dash for the Staten Island ferry, shouting, “Wait! Wait! I lost my Choo.” In that moment, Bradshaw and British footwear brand Jimmy Choo became synonymous, and those looking to emulate her signature look sought out extravagant styles, such as these rhinestone-embellished stilettos; the ballerina tutu and name-plate necklace were optional.
2002 Diane von Furstenberg wrap dress
“What is important is that the woman feels confident and in charge,” says Belgium-born fashion designer Diane von Furstenberg, whose legacy proves that, sometimes, the most uncomplicated ideas are the best. Her famed wrap-dress silhouette has endured for more than four decades, thanks to its ultra-flattering shape and one-and-done simplicity.
2003 Juicy Couture velour hoodie
The unmistakable Juicy Couture velour hoodie long predates the off-duty-style phenomenon. Since its heyday as the original elevated athleisure uniform when it debuted in 2001, the tracksuit (seen here on Halle Berry) has been immortalized in fashion history by the Victoria and Albert Museum in London, which acquired a fluoro-pink version in 2015. It also enjoyed a high-fashion reincarnation on Vetements’ SS17 runway as a skin-tight catsuit and floor-skimming skirt.
2004 Chloé’s banana-print T-shirt
As well as her career-defining stint at Céline, Phoebe Philo’s legacy includes helming Chloé as creative director from 2001 to 2006. While her tenure at the maison is most often associated with her ultra-covetable Chloé ‘It’ bags (more on that to come), she also infused the ready-to-wear with a cool, ultra-feminine flair, as this playful banana-print crop top epitomizes.
2005 Roland Mouret’s Galaxy dress
French designer Roland Mouret debuted his now-iconic Galaxy dress in 2005. Its sexy, second-skin, waist-cinching silhouette was an instant red-carpet hit, garnering Mouret a sizeable celebrity fan base that included Beyoncé (pictured), Rachel Weisz and Meghan Markle – and sealing his reputation as the master of drape and shape.
2006 Chloé’s Paddington bag
One of Phoebe Philo’s most influential moments at Chloé was her creation of the Paddington bag (seen here on the arm of English model Lily Donaldson). Few accessories are quite as deserving of the ‘It’ prefix as this slouchy leather number, with its signature chunky gold padlock. Famously, every one of the 8,000 versions were spoken for following its unveiling on the SS05 runway. Current creative director Natacha Ramsay-Levi recently paid homage to the Paddington with her FW19 Aby bag, replete with logo padlock.
2007 True Religion’s Joey boot-cut jeans
Denim was inescapable in the noughties. The shape of choice was a low-rise boot cut, and one of the most in-demand brands was True Religion. Instantly identifiable by its distinctive horseshoe-stitched back pocket, the Joey jean was a hugely sought-after style. Paired with a chunky leather belt and pointed boots – like Cindy Crawford here – and you’d nailed the look.
2008 Alexander McQueen’s skull scarf
Lee McQueen’s legendary archive is overflowing with iconic pieces, from Shalom Harlow’s spray-painted dress to his 12-inch Armadillo boots. Of his more accessible pieces, however, was the skull scarf. First appearing on his SS03 runway, where it was tied nonchalantly around chunky leather belts, its popularity has endured to this day.
2009 Proenza Schouler’s PS1 bag
New York design duo Proenza Schouler’s PS1 bag blends preppy Upper East Side polish with a touch of Downtown cool. With its pared-back design, the sleek satchel signified a shift towards a low-key, un-logoed era for ‘It’ bags.
2010 Alexander Wang’s Rocco bag
With its grainy leather texture and punky, stud-embellished base, Alexander Wang’s Rocco duffle bag was the epitome of laid-back cool. Its tough-luxe aesthetic fit perfectly with the emerging ‘off-duty model’ look, and it was often spotted swinging from the arm of an Olsen sister (as here).
2011 Saint Laurent’s Arty ring
Saint Laurent’s Arty ring was the ultimate piece of statement jewelry in the early twenty-tens. Crafted from molten gold, with a large oval stone of varying colors, it was a wholly unique piece of costume jewelry, created during Stefano Pilati’s tenure at the French maison.
2012 Acne Studios’ Pistol boots
Timeless, understated and cool, Acne Studios’ Pistol boots lent a touch of Scandi simplicity to late-noughties style and became a pervasive fashion-editor favorite. Unadorned but discreetly identifiable, they marked a step towards utilitarian minimalism.
2013 Givenchy’s Bambi sweatshirt
Though he’s known for his darkly romantic, streetwear-inflected designs, Riccardo Tisci (who was heading up Givenchy at the time) showed his softer side when he sent Bambi down his FW13 runway. His opening look saw the baby deer spliced with an oil-painting motif emblazoned on an oversized black sweatshirt and paired with a sheer knee-length skirt, perfectly espousing the powerfully feminine with the coolly subversive – a Tisci trademark.
2014 Mansur Gavriel’s Bucket bag
The Mansur Gavriel Bucket bag was something of a stealth success story. With a focus on flawless design and unadornment, the capacious drawstring-fastened bag with a boldly colored lining (a black outer with red inner was the combination of choice) and a discreet gold-embossed logo – by an emerging New York-based design duo – was one of those out-of-the-blue trends that suddenly every fashion editor wanted in on.
2015 Anya Hindmarch’s Crisp Packet bag
The Crisp Packet bag is a perfect example of how British designer Anya Hindmarch can turn the ordinary into something extraordinary. Requiring 15 different molds to create, the sculptural evening bag epitomizes the brand’s impeccable craftmanship, as well as its irreverence, and has become a red-carpet classic.
2016 JW Anderson’s Pierce bag
Jonathan Anderson has become a revered purveyor of ultra-desirable handbags, both at his namesake label JW Anderson and at the Spanish house of Loewe. His Pierce bag first appeared in his pre-fall 2016 collection and became a regular on the Fashion Week street-style circuit from then on. It perfectly encapsulates the Irishman’s quietly rebellious nature: the seemingly ladylike shoulder bag is offset by punkish, oversized bar-bell hardware, inspired by a pierced septum.
2017 Castañer’s espadrille wedges
If ever there were a shoe to claim serious style mileage, it’s the Castañer espadrille wedge. Though far less conspicuous than other ‘It’ shoes of the decade (the Valentino Rockstud pumps for one, and Balenciaga’s pumped-up Triple S sneakers for another), the brand’s 93-year heritage and reputation as the maker of a chic and dependable summer shoe cannot go unacknowledged. Founded in 1927 by the Castañer family, who were famously commissioned by Yves Saint Laurent in the ’70s to create a pair of jute-soled wedges, they have gone on to work with many other major fashion houses over the years.
2018 Gucci’s ‘GG’ belt
Of the 45 Baroque, ruffled and brightly-colored looks in Alessandro Michele’s AW15 Gucci debut, the simple black interlocking Gs belt in the opening look has gone on to become one of the designer’s most popular items. Alongside Gucci’s much-loved Dionysus and Marmont bags, and preppy-chic Horsebit loafers, the belt’s ubiquity on the street – where it’s been worn simply with jeans, or to cinch the house’s printed day dresses and pleated midi skirts – has no doubt amplified its enduring popularity.
2019 The Row’s Bare sandals
A good pedicure is a prerequisite for The Row’s elegant Bare sandal, with its whip-thin straps. The minimalist mid-heeled shoe, which comes in multiple colorways, is the perfect transitional piece, adding a polished feel to day dresses and a pared-back elegance to eveningwear. This one has been a big hit at NET-A-PORTER HQ, with global buying director Elizabeth von der Goltz and four of her team members showing up to the SS19 shows at New York Fashion Week all wearing different color variations of the cult kitten heel.
2019 bonus entry: Khaite’s cashmere bra and cardigan
Though it only appeared in the latter half of 2019, it is impossible not to mention the cashmere cardigan and bra that sold out within the hour after Katie Holmes was pictured wearing it on the streets of New York last August. Credited to emerging brand Khaite – the label loved for its luxe basics – it shone a light on designer Catherine Holstein, who was already gaining huge traction with fashion-industry insiders.
2020 Bottega Veneta’s Pouch bag
The hype surrounding Bottega Veneta’s creative director is not undeserved. Daniel Lee arrived at the brand via Celine in July 2018 and has injected the Italian heritage house with his refined vision and mastery of color while staying true to its signatures, including its trademark intrecciato leather technique. Lee is only just getting started, but his softly structured, grab-and-go Pouch bag has already become one of his most popular pieces, and a contributing factor to his Accessories Designer of the Year win at the Fashion Awards in London last December. Lee also scooped British Womenswear Designer of the Year, Brand of the Year and Designer of the Year on the night. As we said, the hype is justified.
The people featured in this story are not associated with NET-A-PORTER and do not endorse it or the products shown